


The Arrangement

by aly_m_cap



Series: The Arrangement [1]
Category: Supernatural
Genre: Caring John Winchester, F/M, Sugar baby Reader, Supernatural Fluff, Supernatural smut, businessman john winchester, sugar daddy john winchester, supernatural angst
Language: English
Status: In-Progress
Published: 2019-05-31
Updated: 2019-05-31
Packaged: 2020-04-05 05:09:06
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19041772
Author URL: https://archiveofourown.org/users/aly_m_cap/pseuds/aly_m_cap
Summary: Dating apps were never your thing, especially the one that you had met Mr. John Winchester on. A rich, older, successful business man wanted your company in return for money. It was something a young and poor girl couldn’t pass up. But, the relationship changed in ways neither one of you thought would happen.





	The Arrangement

You sighed as you tugged at your dress in the full-length mirror that was hanging over your bedroom door. Your phone chimed from your bed, causing you to jump towards whatever notification it would be.

You had a feeling you knew who it was.

You clicked your home button, the blackened screen illuminating and revealing your notification. 

SeekingArrangement: John Winchester sent you a message.

Your stomach dropped as you unlocked your phone, hoping he hadn’t changed his mind. You exhaled with relief as you read his message. ‘MY DRIVER SHOULD BE THERE IN FIVE MINUTES. I’LL SEE YOU AT THE RESTAURANT.’

You bit at your glossed lip in excitement before locking your phone and throwing it in your purse. You grabbed the black, faux leather bag and put it over your shoulder as you began to walk out of your bedroom. You stopped in front of the mirror, checking over your appearance once more. Satisfied, you took a deep breath and walked out towards your living room.

Looking out your front window, a black Cadillac Escalade with tinted windows pulled up in front of your rental and honked. You gripped your purse straps tightly as you walked to your front door. Taking one last deep breath, you opened the door and locked it before walking towards the ominous vehicle.

You opened the back door, saying a soft and half-assed prayer to yourself that you weren’t about to get into a strangers car and get murdered. As you settled into the back seat, the driver pulled away from the curb and talked to you in the rearview mirror. “Hello Miss. Y/L/N. I’m Levi, Mr. Winchester’s personal driver. He’s already waiting for you at the restaurant, so I’ll make sure I get you there quickly and safely.”

You smiled and nodded, “Thank you Levi.”

He nodded towards you in the mirror and continued driving in silence.

You watched the scenery of your neighborhood pass by you in a slight blur. You nervously picked at the hem of your dress as you noticed the part of town you were going in to. The Upper East Side. The rich, upper class side of town. Your nerves began to get the best of you as you studied the area.

You’d only been in this section of town once, when you first moved to New York City. You had gone in for an interview at one of the coffee shops, just hoping for some sort of job at the time. You were 18 and young, just looking for anything to keep you somewhat afloat. You ended up getting a receptionists job in your neighborhood and never stepped foot in the Upper East Side again.

Levi pulled up to the Flora Bar and looked in the rearview mirror once more to talk to you as he parked. “Mr. Winchester is inside.”

You nodded as you grabbed your purse and slid out of the Escalade. You gulped as you looked into the towering, floor to ceiling windows of the pricey establishment. Taking small, even breaths to keep your nerves down, you walked towards the front doors of the bar.

The hostess greeted you with a small smile, “Welcome to Flora Bar! Dining alone tonight?”

You shook your head, “I’m here to meet someone. Mr.-Mr. Winchester.” You scolded your nerves for making you stumble over your words but the hostess didn’t seem to notice.

“Oh,” she paused with a knowing look in her eyes, “Follow me!” She chirped. “I’ll take you to Mr. Winchester.”

You followed her with a nervous smile and a white knuckled grip on your purse strap. You focused on your breathing as you walked through the restaurant. The hostess lead you through doors in the back of the restaurant, opening up to a private room, seating the one and only: Mr. John Winchester.

She smiled towards you as she turned and walked out of the room. You bit at your lip as you walked towards the small table John sat at.

He smiled, his eyes crinkling in the corners, as he got up from the table. “Y/N.” He bit at his lip, “My, my, my. Don’t you look absolutely breathtaking tonight.”

You could feel your cheeks flush from the adulation, causing you to giggle softly from the compliment, “Thank you Mr. Winchester.” You eyed the 6’1”, hazel-eyed, suit-clad, business man. His suit clung to his body in all the right places, accentuating his muscular, tall form. “You look…,” you paused and looked towards his face, a large smile hiding behind his salt and peppered beard, “amazing yourself.”

He let out a deep, rumbling chuckle as he winked at you, “I don’t look as good as you though, sweetheart.” He turned towards the table and pulled out your chair, “M’lady,” he drawled.

You giggled once more at his small form of humor as you sat at the table. You glanced at what you could see on the menu in front of you, nearly choking at the prices of the food. John rounded the table and sat across from you. You smiled towards him as he settled in his chair and looked towards you, studying you.

He cleared his throat without breaking eye contact. “So, Y/N. What do you want to do first? Talk and get to know each other a little bit or start negotiating our deal?”

In that moment, all your worries and nerves washed away as you watched John. His calm, yet slightly cocky demeanor paired with previous humor eased your mind about this new form of ‘dating’ you were experiencing. “Let’s talk for a bit. See if we have good chemistry before we start negotiating our deal.” You looked down towards the menu, picking it up and looking over the first page before settling your eyes back towards him. “Because,” you motioned between you both, “this won’t work if we don’t.”

John’s tongue peaked out, wetting his bottom lip slightly as a shit-eating grin spread across his face, “You’re right, sweetheart.” He sat forward, leaning over the table towards you, “This won’t work if we don’t.” His front teeth bit down lightly on his bottom lip as his gaze seemed to burn through your soul, “But, I can already tell that we’ll have great chemistry.”

You raised a brow slightly as you looked over the menu at him. “Oh yeah?” You laid the menu back on the table slowly before leaning on the table towards John, “Why do you say that?”

He leaned back in his chair with his cocky grin in place, “For one,” he rubbed his hand down his beard, “you aren’t afraid of me. Most girls were when we met, hence why I’m still looking for my sugar baby.” His eyes glistened with mischief as he continued to watch you, “You’re different. Different than the rest. I like that.”

You picked up the menu again, redirecting your attention from the silvering fox to the laminated paper. “I suppose we will just have to see, Mr. Winchester.” With a sly grin creeping up on your face, you thought ‘I think you’ll find out that I’m just as much trouble as you.’

Johns smile widened. “I guess we will, sweetheart,” he said with his gravelly voice as he winked in your direction


End file.
